Discussion
Which one of the following compounds is strongly basic in aqueous medium?
Answer: B
The strongly basic compound is N-ethylethanamine (diethylamine).
Aliphatic amines are stronger bases than ammonia, because alkyl groups push electron density onto the nitrogen. In water, secondary amines such as diethylamine are the strongest, owing to the combined effect of electron release and solvation of the ammonium ion.
In benzenamine (aniline) and N,N-dimethylbenzenamine the nitrogen's lone pair is delocalised into the ring, making them much weaker bases than ammonia. Phenylmethanamine (benzylamine) is a primary amine, weaker than diethylamine, and ammonia is weaker than both aliphatic amines.
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